Abstract
A rapid method has been developed for the synthesis of benzothiazoles via the condensation of 2-aminothiophenol with aldehydes under CEM-focused microwave irradiation conditions. The reaction used glycerol as a green solvent without any catalyst, rendering this methodology valuable from both economic and environmental points of view.
References
1.
Oksuzoglu E.
,
Temiz-Arpaci O.
,
Tekiner-Gulbas B.
,
Eroglu H.
,
Sen G.
,
Alper S.
,
Yildiz I.
,
Diril N.
,
Aki-Sener E.
, and
Yalcin I.
, Med. Chem. Res. , 2008 , 16 , 1 .
2.
Hranjec M.
,
Kralj M.
,
Piantanida I.
,
Sedic M.
,
Suman L.
,
Pavelic K.
, and
Karminski-Zamola G.
, J. Med. Chem. , 2007 , 50 , 5696 .
3.
Grobler J.A.
,
Dornadula G.
,
Rice M.R.
,
Simcoe A.L.
,
Hazuda D.J.
, and
Miller M.D.
, J. Biol. Chem. , 2007 , 282 , 8005 .
4.
Riadi Y.
,
Mamouni R.
,
Azzalou R.
,
El Haddad M.
,
Routier S.
,
Guillaumet G.
, and
Lazar S.
, Tetrahedron Lett. , 2011 , 52 , 3492 .
5.
Fan X.
,
He Y.
,
Wang Y.
,
Xue Z.
,
Zhang X.
, and
Wang J.
, Tetrahedron Lett. , 2011 , 52 , 899 .
6.
Bandyopadhyay P.
,
Sathe M.
,
Prasad G.K.
,
Sharma P.
, and
Kaushik M.P.
, J. Mol. Catal. A: Chem. 2011 , 341 , 77 .
7.
Seijas J.A.
,
Vázquez-Tato M.P.
,
Carballido-Reboredo M.R.
,
Crecente-Campo J.
, and
Romar-López L.
, Synlett , 2007 , 313 .
8.
Bahrami K.
,
Khodaei M.M.
, and
Naali F.
, Synlett , 2009 , 569 .
9.
Khan K.M.
,
Rahim F.
,
Halim S.A.
,
Taha M.
,
Khan M.
,
Perveen S.
,
Mesaik M.A.
, and
Choudhary M.I.
, Bioorg. Med. Chem. , 2011 , 19 , 4286 .
10.
Cohen V.I.
, and
Pourabass S.
, J. Heterocycl. Chem. , 1977 , 14 , 1321 .
11.
Boger D.E.
, J. Org. Chem. , 1978 , 43 , 2296 .
12.
Abbotto A.
,
Bradnmante S.
,
Facchetti A.
, and
Pagani G.A.
, J. Org. Chem. , 2002 , 67 , 5753 .
13.
Candeias N.R.
,
Branco L.C.
,
Gois P.M.P.
,
Afonso C.A.M.
, and
Trindade A.F.
, Chem. Rev. , 2009 , 109 , 2703 .
14.
Walsh P.J.
,
Li H.
, and
De Parrodi C.A.
, Chem. Rev. , 2007 , 107 , 2503 .
15.
Martins M.A.P.
,
Frizzo C.P.
,
Moreira D.N.
,
Buriol L.
, and
Machado P.
, Chem. Rev. , 2009 , 109 , 4140 .
16.
Pagliaro M.
, and
Rossi M.
, The future of glycerol: new usages for a versatile raw material , RSC Publishing , Cambridge , 2008 .
17.
Gu Y.
, and
Jérôme F.
, Green Chem. , 2010 , 12 , 1127 .
18.
Díaz-álvarez A.
,
Feancos J.
,
Lastra-Barreira B.
,
Crochet P.
, and
Cadierno V.
, Adv. Synth. Catal. , 2011 , 47 , 6208 .
19.
Appukkuttan P.
,
Mehta V.P.
, and
Van der Eycken P.
, Chem. Soc. Rev. , 2010 , 39 , 1467 .
20.
Polshettiwar V.
, and
Varma R.S.
, Green Chem. , 2010 , 12 , 743 .
21.
Kappe C.O
, and
Van der Eycken E.
, Chem. Soc. Rev. , 2010 , 39 , 1280 .
22.
Bai L.
, and
Wang J.-X.
, Adv. Synth. Catal. , 2008 , 350 , 315 .
23.
Henry C.
,
Haupt A.
, and
Turner S.C.
, J. Org. Chem. , 2009 , 74 , 1932 .
24.
Caddick S.
, and
Fitzmaurice R.
, Tetrahedron , 2009 , 65 , 3325 .
25.
Zhou W.-J.
,
Wang K.-H.
, and
Wang J.-X.
, J. Org. Chem. , 2009 , 74 , 5599 .
26.
Shi W.
, and
Wang J.-X.
, J. Chem. Res. , 2008 , 270 .
27.
Wang J.-X.
,
Xi Y.
,
Wu X.
,
Hu Y.
, and
Du Z.
, Synth. Commun. , 1998 , 28 , 4619 .
28.
Evindar G.
, and
Batey R.A.
, J. Org. Chem. , 2006 , 71 , 1802 .
29.
Belgodere E.
,
Bossio R.
,
Chimichi S.
,
Parrini V.
, and
Pepino R.
, Dyes Pigments , 1983 , 1 , 59 .
30.
Brembilla A.
,
Roizard D.
, and
Lochon P.
, Synth. Commun. , 1990 , 21 , 3379 .
31.
Anthony K.
,
Brown R.G.
,
Hepworth J.D.
,
Hodgson K.W.
,
May B.
, and
West M.A.
, J. Chem. Soc. Perkin Trans. , 1984 , 2111 .
32.
Bogert M.T.
, and
Corbitt H.B.
, J. Am. Chem. Soc. , 1926 , 48 , 783 .
33.
Maleki B.
, Collect. Czech. Chem. Commun. , 2011 , 76 , 27 .
34.
Melnikova E.B.
,
Elchaninov M.M.
,
Milov A.A.
, and
Lukyanov B.S.
, Chem. Heterocylic. Comp. , 2008 , 44 , 1070 .